While slamming a girl in the ass, pull out as soon as her crap is comming out.
Drag your dick from her anus, through her ass crack, between her tits and to her mouth, while making sure you leave a solid trail of shit over her body.
Celebrate the end of the journey with a rough deep throat.
"I gave Sally the good old Oregon Trail last month, but she died of cholera after the journey."
by ColonelPrittius March 22, 2018
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The act of snorting Cocaine down a torso, drinking a belly shot, then preforming Oral Sex on a partner with a known STD in one continuous act.
I have Herpes now from walking the Oregon Trail with a stripper.
by Pongluver January 24, 2010
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As an out of state resident, the first line of legal cocaine you insufflate upon your arrival in Oregon.
Yo I blew a massive Oregon Trail after crossing into Oregon for the first time in 2020. So tweaked rn.
by C Chaotic November 14, 2020
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In bowling, getting three strikes in the tenth frame. The first strike is gathering the supplies, the second strike is forging the river, the final strike gets you over the rocky mountains and completes the oregon trail.
Josh just got an oregon trail. He needed it to break 200
by bowlermaniac June 22, 2011
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When ur fuckin a girl doggy style & u bust a monster load on the small of her back & when she stands up the jizz runs down her ass crack
My girl wouldnt let me jizz in her mouth so i gave her an oregon trail instead
by Bb&cv July 8, 2010
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1)Penetrate the anal cavity.

2) To then rub the genitalia across the vaginal region and across her stomach (the Great Plains) moving forward to the Rockies (her chest) and park your wagon in her mouth, leaving a brown trail.
when your having sex and you make a trail of poop. The Oregon Trail. Have you ever ridden on the oregon trail?
by Trail Master July 20, 2008
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the cave in Blood Gulch left of Domination Hill with the overshield in it.
Frick! he's in the Oregon!
by Ryo March 29, 2004
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